Patent EP-0174832-A3 (EP)
IPC: A61P29/00
Filed: 1985-09-10
Abstract: Ethene derivatives of the general formula:  
[R⁵(R¹CR⁴=CR²R³) m ] n  (1)  
wherein R⁵ represents a heterocyclyl group, containing 1,2 
or 3 rings and one or more heteroatoms selected from 
nitrogen, oxygen, sulphur and selenium atoms, which 
unsubstituted or substituted by one or more substituents 
[which may be the same or different and each represents 
halogen atom or an amino, carboxy, cyano, nitro, hydroxy, 
oxo, formyl, trifluoromethyl, aryl, aryloxy, arylthio, benzy­
loxycarbonylamino, sulphanoyl, tetrazoyl-5-yl, carbamoyl, 
thiocarbamoyl, arylcarbamoyl or aroyl group, or a straight- 
or branched-chain alkyl group containing from 1 to 10 carbon 
atoms, or a straight- or branched-chain alkoxy, alkylthio, 
alkylsulphinyl, alkylsulphonyl, alkylamino, alkylsulphamoyl, 
arylalkyl or arylalkoxy group containing from 1 to 10 carbon 
atoms in the alkyl moiety, a straight- or branched-chain 
alkanoyl, alkoxycarbonyl, alkoxycarbonylamino, alkylcarba­
moyl or alkanoylamino group containing from 2 to 6 carbon 
atoms, a N-benzyloxycarbonyl-N-alkylamino group where­
in the alkylamino moiety is straight- or branched-chain and 
contains from 1 to 6 carbon atoms, or a dialkylsulphamoyl, 
dialkylamino or dialkylcarbamoyl group wherein the alkyl 
moieties may be straight or branched and may each contain 
from 1 to 6 carbon atoms and may be linked together to form 
a ring, or a group of the formula -CR⁴=CR²R³, or an aryl 
group which is unsubstituted or substituted by one or more 
substituents R⁸ (as hereinbefore defined), or a heterocyclylal­
kyl or aryalkyl group wherein the heterocyclyl or aryl moiety 
is as hereinbefore defined and the alkyl moiety is straight- or 
branched-chained and contains 1 or 2 carbon atoms, and R¹ 
represents a group of the general formula:  
-NR⁶- II  
wherein R⁶ represents a hydrogen atom or a straight- or 
branched-chain alkyl group containing from 1 to 6 carbon 
atoms which may be substituted by one or more substituents 
R⁸ (as hereinbefore defined) or an aryl group which may be 
substituted by one or more substituents R⁸ (as hereinbefore 
defined), or R⁵ represents a quinonoidal group R⁷ derived 
from a nitrogen-containing heterocyclyl group within the 
definition of R⁵ as hereinbefore defined, bearing on said 
ring-nitrogen atom a substituent selected from straight- and 
branched-chain alkyl groups containing from 1 to 6 carbon 
atoms which may be substituted by one or more substituents 
R⁸ (as hereinbefore defined), and aryl groups which may be 
substituted by one or more substituents R⁸ (as hereinbefore 
defined), and R¹ represents an atom =N-, R⁴ represents a 
hydrogen atom or a straight- or branched-chain alkoxy or 
alkylthio group containing from 1 to 6 carbon atoms, a 
trifluoromethyl group or a straight- or branched-chain alkyl 
group containing from 1 to 6 carbon atoms which may be 
substituted by one or more substituents R⁸ (as hereinbefore 
defined), or an aryl group which may be substituted by one 
or more substituents R⁸ (as hereinbefore defined), R² 
represents a cyano or formyl group, a straight- or branched-­
chain alkoxycarbonyl or alkylsulphonyl group containing up 
to 6 carbons, or a dialkylcarbamoyl or dialkylthiocarbamoyl 
group wherein the alkyl groups may be the same or different 
and each may be straight or branched and each contains 
from 1 to 6 carbon atoms, or an aryloxycarbonyl, arylsul­
phinyl or arylsulphonyl group wherein the aryl moiety may 
be substituted by one or more substituents R⁸ (as hereinbe­
fore defined), R³ represents a group within the definition of 
R² or a hydrogen atom or a nitro group or an aryl or aroyl 
group which may be substituted by one or more substituents 
R⁸ (as hereinbefore defined) or a straight- or branched-chain 
alkanoyl group containing up to 6 carbon atoms, and m and 
n each represents 1 or 2, and pharmaceutically acceptable 
salts thereof, with the provisos that the following classes of 
compounds are excluded:-  
(i) compounds of formula I wherein R⁵ represents a 
pyridyl group which is unsubstituted or substituted by one or 
more substituents R⁹ which may be the same or different and 
each represents a group within the definition of R⁸ other than 
oxo, straight- or branched-chain alkyl containing from 7 to 10 
carbon atoms, straight- or branched-chain alkoxy, alkylthio, 
alkylsulphonyl, alkylamino, alkylsulphamoyl or arylalkyl con­
taining from 7 to 10 carbon atoms in the alkyl moiety, 
straight- or branched-chain alkylsulphinyl or arylalkoxy 
containing from 1 to 10 carbon atoms in the alkyl moiety, or a 
group -CR⁴=CR²R³as hereinbefore defined, R² and R³ may 
be the same or different and each represents a phenylsul­
phonyl group which may be unsubstituted or substituted by 
one or more substituents R⁹ (as hereinbefore defined), R¹ 
represents a group of formula II, R⁴ and R⁶ represent 
hydrogen atoms and m and n both represent 1;  
(ii) compounds of formula I wherein R⁵ represents a 
5-halogenopyrid-2-yl group, R² and R³ both represent cyano 
groups, R¹ represents a group of formula II, R⁴ and R⁶ 
represent hydrogen atoms and m and n both represent 1; 
and  
(iii) compounds of formula I wherein R⁵ represents a 
1,2,4-triazolo[4,3-a]-quinoline group which is unsubstituted 
or substituted by one or more substituents R¹⁰ which may be 
the same or different and each represents a group within the 
definition of R⁹ or a straight- or branched-chain alkylsul­
phinyl group containing from 1 to 6 carbon atoms, R² and R³ 
may be the same or different and each represents a cyano 
group, a straight- or branched-chain alkoxycarbonyl group 
containing from 2 to 6 carbon atoms, or a phenylsulphonyl 
group which may be unsubstituted or substituted by one or 
more substituents R¹⁰ (as hereinbefore defined), R¹ repre­
sents a group of formula II, R⁴ and R⁶ represent hydrogen 
atoms and m and n both represent 1, possess useful 
pharmacological properties.